N-[4-Acetyl-5-isobutyl-5-(2-p-tolyl­prop­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide ethyl acetate hemisolvate

Loughzail, M.; Mazoir, N.; Maya, C.M.; Berraho, M.; Benharref, A.; Bouhmaida, N.

doi:10.1107/S1600536808039998

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o4

doi:10.1107/S1600536808039998

Open

access

N-[4-Acetyl-5-isobutyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide ethyl acetate hemisolvate

Mohamed Loughzail,^a Noureddine Mazoir,^a Celia M. Maya,^b Moha Berraho,^c Ahmed Benharref ^a and Nouzha Bouhmaida ^d ^*

^aLaboratoire de Chimie des Substances Naturelles, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, ^bInstituto de Química Física Rocasolano, Consejo Superior de Investigaciones Científicas, Serrano 119, 28002 Madrid, Spain, ^cLaboratoire de Chimie de Coordination, Unité Matériaux, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^dLaboratoire des Sciences des Matériaux, Département de Physique, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
^*Correspondence e-mail: nouzha@ucam.ac.ma

(Received 28 October 2008; accepted 27 November 2008; online 3 December 2008)

The racemic title compound, a new terpenoid, C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂, was synthesized from Cedrus Atlantica essential oil. The compound crystallizes with a disordered ethyl acetate solvent molecule. The thiadiazole ring is almost planar, with a maximum deviation from the mean plane of 0.015 (2) Å for the C atom connected to the isobutyl group and has a puckering amplitude of 0.026 (2) Å. The dihedral angle between the benzene and thiadiazole rings is 18.32 (8)°. The crystal packing involves intermolecular N—H⋯O hydrogen bonds.

Related literature

For 1,3,4-thiadiazole derivatives and their biological activity, see: Abdou et al. (1991 ); Sakthivel et al. (2008 ); Tehranchian et al. (2005 ); Wang et al. (1999 , 2004 ). For preparative methods, see: Beatriz et al., 2002 ; Mohammed et al. (2008 ); For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂
M_r = 419.57
Monoclinic, P 2₁ /n
a = 7.8713 (3) Å
b = 12.7587 (5) Å
c = 22.9688 (9) Å
β = 90.937 (2)°
V = 2306.39 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 295 K
0.5 × 0.4 × 0.3 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer
Absorption correction: none
27541 measured reflections
7243 independent reflections
6688 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.143
S = 1.23
7243 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.95	2.812 (2)	179
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039998/fj2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039998/fj2168Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives (Sakthivel et al., 2008) are associated with diverse activities: fungicidal (Abdou et al., 1991), pesticidal (Wang et al., 1999, 2004) and bactericidal (Tehranchian et al., 2005) properties.

As part of our ongoing valorization of Cedrus species native to the Medium-Atlas Mountains of Morocco, we have investigated the crystal structure of semi-synthetic terpenoid derivatives obtained through chemical modifications of 1-(4-methylcyclohex-3-enyl) ethanone (I). The latter is isolated from Cedrus Atlantica essential oil. The aromatization of (I) followed by condensation with thiosemicarbazide (Beatriz et al., 2002; Mohammed et al., 2008) ending with treatment by acetic anhydride in the presence of pyridine yielded the compound diastereoisomers in high stereoselectivity.

The title compound molecular structure is shown in figure 1. The solvant molecule is located on the inversion site and disordered. The thiadiazole ring is almost planar with a maximum deviation from the mean plane of 0.015 (2)Å for the C atoms connected to the isobutyl group and a puckering amplitude of 0.026 (2)Å (Cremer & Pople, 1975). Hydrogen bonds are listed in table 1. Investigation of the crystal packing reveals an intermolecular N1—H1···O2 hydrogen bonding generating parallel chains to b axis as shown in figure 2.

Related literature top

For 1,3,4-thiadiazole derivatives and their biological activity, see: Abdou et al. (1991); Sakthivel et al. (2008); Tehranchian et al. (2005); Wang et al. (1999,2004). For preparative methods, see: Beatriz et al., 2002; Mohammed et al. (2008); For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A solution of 1-(4-methylcyclohex-3-enyl) ethanone (1 g, 4.5 mmol) and Pd/C (10%) were heated at 150°C during 12 h. The product obtained was treated with equimolecular quantity of thiosemicarbazide and several drops of HCl (cc) were added. The reactional mixture was heated at reflux in ethanol for 5 h and then evaporated under reduced pressure and the residue obtained was purified on silica gel column using hexane-ethyl acetate (95:5) as an eluent. 0.25 mmol of the thiosemicarbazone obtained was dissolved in 2 ml of pyridine and 2 ml of acetic anhydride. The mixture was heated on a water bath during 1 h. The resulting residue was concentrated in vacuo and chromatographied on silica gel column with hexane-ethyl acetate (90:10) as an eluent. Suitable crystals were obtained by evaporation of ethyl acetate solution at 277 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. : Molecular structure shown with the atom-labelling scheme. Thermal ellipsoids are drawn at the 30% probability displacement. H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. : The crystal packing showing the molecules connected by N–H···O hydrogen bondings (dashed lines). H atoms not involved in hydrogen bonding have been omitted.

N-[4-Acetyl-5-isobutyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol- 2-yl]acetamide ethyl acetate hemisolvate top

Crystal data top

C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂	F(000) = 904
M_r = 419.57	D_x = 1.208 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13322 reflections
a = 7.8713 (3) Å	θ = 2.6–31.5°
b = 12.7587 (5) Å	µ = 0.17 mm⁻¹
c = 22.9688 (9) Å	T = 295 K
β = 90.937 (2)°	Prism, colourless
V = 2306.39 (16) Å³	0.5 × 0.4 × 0.3 mm
Z = 4

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	6688 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 32.0°, θ_min = 1.8°
ϕ and ω scans	h = −11→11
27541 measured reflections	k = −16→18
7243 independent reflections	l = −33→30

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.0435P)² + 1.5861P] where P = (F_o² + 2F_c²)/3
7243 reflections	(Δ/σ)_max = 0.006
298 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂	V = 2306.39 (16) Å³
M_r = 419.57	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8713 (3) Å	µ = 0.17 mm⁻¹
b = 12.7587 (5) Å	T = 295 K
c = 22.9688 (9) Å	0.5 × 0.4 × 0.3 mm
β = 90.937 (2)°

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	6688 reflections with I > 2σ(I)
27541 measured reflections	R_int = 0.037
7243 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.23	Δρ_max = 0.48 e Å⁻³
7243 reflections	Δρ_min = −0.35 e Å⁻³
298 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1'	0.5624 (2)	0.56734 (16)	0.09954 (8)	0.0284 (4)
H1'	0.6130	0.5214	0.0736	0.034*
C2	0.6060 (2)	0.80786 (11)	0.33245 (7)	0.0160 (3)
C2'	0.5345 (2)	0.53523 (13)	0.15666 (8)	0.0231 (3)
H2'	0.5671	0.4681	0.1680	0.028*
C3	0.4619 (2)	0.92243 (12)	0.40282 (7)	0.0189 (3)
C3'	0.4581 (2)	0.60205 (12)	0.19769 (7)	0.0198 (3)
C4'	0.4129 (2)	0.70239 (13)	0.17921 (8)	0.0261 (4)
H4'	0.3636	0.7488	0.2052	0.031*
C4	0.4186 (2)	1.03550 (13)	0.41486 (8)	0.0247 (3)
H41	0.3953	1.0710	0.3788	0.037*
H42	0.5127	1.0687	0.4345	0.037*
H43	0.3202	1.0387	0.4389	0.037*
C5	0.6899 (2)	0.61643 (11)	0.31921 (7)	0.0163 (3)
C5'	0.4414 (3)	0.73375 (16)	0.12186 (9)	0.0334 (4)
H5'	0.4100	0.8011	0.1105	0.040*
C6'	0.5158 (3)	0.66697 (17)	0.08093 (9)	0.0316 (4)
C6	0.5755 (2)	0.53023 (11)	0.29360 (7)	0.0168 (3)
H61	0.6439	0.4869	0.2684	0.020*
H62	0.5382	0.4862	0.3254	0.020*
C7'	0.5422 (3)	0.6998 (2)	0.01806 (10)	0.0496 (6)
H71'	0.4499	0.6741	−0.0058	0.074*
H72'	0.6472	0.6711	0.0046	0.074*
H73'	0.5461	0.7749	0.0157	0.074*
C7	0.4196 (2)	0.56528 (12)	0.25922 (7)	0.0199 (3)
H7	0.3686	0.6241	0.2801	0.024*
C8	0.2898 (2)	0.47506 (15)	0.25783 (9)	0.0280 (4)
H81	0.2646	0.4544	0.2969	0.042*
H82	0.3363	0.4165	0.2372	0.042*
H83	0.1874	0.4980	0.2384	0.042*
C9	0.8420 (2)	0.56432 (12)	0.34917 (7)	0.0203 (3)
H91	0.7995	0.5074	0.3728	0.024*
H92	0.9113	0.5332	0.3192	0.024*
C10	0.9575 (2)	0.63119 (15)	0.38756 (8)	0.0260 (4)
H10	0.8883	0.6640	0.4176	0.031*
C11	1.0522 (2)	0.71819 (16)	0.35485 (11)	0.0358 (5)
H111	0.9721	0.7695	0.3410	0.054*
H112	1.1105	0.6883	0.3224	0.054*
H113	1.1330	0.7510	0.3807	0.054*
C12	1.0842 (3)	0.55835 (18)	0.41726 (9)	0.0389 (5)
H123	1.0243	0.5062	0.4390	0.058*
H121	1.1563	0.5980	0.4432	0.058*
H122	1.1522	0.5247	0.3884	0.058*
C41	0.8340 (2)	0.67172 (12)	0.22639 (7)	0.0182 (3)
C42	0.8709 (3)	0.75771 (13)	0.18334 (8)	0.0259 (4)
H423	0.7761	0.8050	0.1811	0.039*
H421	0.8894	0.7276	0.1457	0.039*
H422	0.9707	0.7953	0.1958	0.039*
O1	0.42441 (18)	0.85144 (10)	0.43626 (6)	0.0281 (3)
O2	0.88630 (16)	0.58120 (9)	0.21879 (5)	0.0211 (2)
N1	0.54896 (18)	0.90516 (10)	0.35115 (6)	0.0174 (3)
H1	0.5686	0.9585	0.3294	0.021*
N3	0.69220 (17)	0.80070 (9)	0.28451 (6)	0.0169 (3)
N4	0.74060 (18)	0.69617 (9)	0.27477 (6)	0.0167 (3)
S1	0.56524 (5)	0.69427 (3)	0.372883 (17)	0.01838 (10)
C1"	0.4182 (8)	0.3287 (4)	0.4750 (2)	0.0377 (11)	0.50
H13"	0.4099	0.3038	0.4357	0.057*	0.50
H12"	0.3115	0.3184	0.4939	0.057*	0.50
H11"	0.5055	0.2906	0.4956	0.057*	0.50
C2"	0.4610 (5)	0.4425 (3)	0.47503 (16)	0.0282 (7)	0.50
C3"	0.4243 (5)	0.6083 (3)	0.52319 (18)	0.0325 (8)	0.50
H32"	0.3404	0.6396	0.5483	0.039*	0.50
H31"	0.4071	0.6367	0.4844	0.039*	0.50
C4"	0.5952 (7)	0.6366 (4)	0.5446 (3)	0.0398 (11)	0.50
H42"	0.6142	0.6066	0.5825	0.060*	0.50
H43"	0.6046	0.7115	0.5470	0.060*	0.50
H41"	0.6784	0.6101	0.5182	0.060*	0.50
O1'	0.5439 (5)	0.4867 (3)	0.43748 (15)	0.0456 (8)	0.50
O2'	0.3987 (4)	0.4949 (2)	0.52147 (12)	0.0326 (6)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1'	0.0218 (9)	0.0388 (10)	0.0247 (9)	0.0006 (7)	−0.0002 (7)	0.0008 (7)
C2	0.0157 (7)	0.0133 (6)	0.0190 (7)	−0.0004 (5)	0.0000 (5)	0.0009 (5)
C2'	0.0214 (8)	0.0239 (7)	0.0239 (8)	0.0030 (6)	−0.0013 (6)	0.0002 (6)
C3	0.0168 (7)	0.0191 (7)	0.0209 (7)	0.0015 (5)	0.0023 (6)	−0.0008 (5)
C3'	0.0163 (7)	0.0189 (7)	0.0241 (8)	0.0009 (5)	−0.0036 (6)	0.0012 (6)
C4'	0.0244 (9)	0.0213 (7)	0.0324 (9)	0.0032 (6)	−0.0063 (7)	0.0017 (6)
C4	0.0287 (9)	0.0182 (7)	0.0274 (9)	0.0056 (6)	0.0075 (7)	−0.0016 (6)
C5	0.0182 (7)	0.0141 (6)	0.0167 (7)	0.0015 (5)	0.0033 (5)	0.0001 (5)
C5'	0.0314 (10)	0.0288 (9)	0.0396 (11)	−0.0015 (7)	−0.0097 (8)	0.0128 (8)
C6'	0.0237 (9)	0.0410 (10)	0.0300 (10)	−0.0049 (8)	−0.0027 (7)	0.0118 (8)
C6	0.0168 (7)	0.0140 (6)	0.0197 (7)	0.0003 (5)	0.0030 (6)	0.0012 (5)
C7'	0.0455 (14)	0.0672 (17)	0.0360 (12)	−0.0024 (12)	0.0003 (10)	0.0221 (11)
C7	0.0163 (7)	0.0200 (7)	0.0236 (8)	0.0021 (6)	0.0019 (6)	−0.0017 (6)
C8	0.0194 (8)	0.0341 (9)	0.0304 (9)	−0.0049 (7)	0.0026 (7)	0.0002 (7)
C9	0.0213 (8)	0.0194 (7)	0.0201 (7)	0.0027 (6)	−0.0006 (6)	−0.0008 (5)
C10	0.0198 (8)	0.0319 (9)	0.0263 (9)	0.0054 (7)	−0.0023 (7)	−0.0096 (7)
C11	0.0186 (9)	0.0334 (9)	0.0552 (13)	−0.0012 (7)	−0.0059 (9)	−0.0046 (9)
C12	0.0381 (12)	0.0469 (12)	0.0312 (10)	0.0131 (9)	−0.0140 (9)	−0.0090 (9)
C41	0.0189 (7)	0.0165 (6)	0.0192 (7)	−0.0032 (5)	0.0020 (6)	−0.0025 (5)
C42	0.0341 (10)	0.0189 (7)	0.0252 (8)	−0.0031 (6)	0.0116 (7)	−0.0002 (6)
O1	0.0367 (8)	0.0199 (5)	0.0280 (7)	0.0030 (5)	0.0130 (6)	0.0025 (5)
O2	0.0224 (6)	0.0179 (5)	0.0231 (6)	0.0007 (4)	0.0039 (5)	−0.0040 (4)
N1	0.0207 (7)	0.0137 (5)	0.0179 (6)	0.0020 (5)	0.0031 (5)	0.0003 (4)
N3	0.0182 (6)	0.0126 (5)	0.0200 (6)	−0.0002 (5)	0.0020 (5)	−0.0003 (4)
N4	0.0202 (6)	0.0126 (5)	0.0175 (6)	−0.0004 (5)	0.0037 (5)	−0.0007 (4)
S1	0.0229 (2)	0.01389 (16)	0.01860 (18)	0.00144 (13)	0.00611 (14)	0.00131 (12)
C1"	0.057 (3)	0.029 (2)	0.027 (2)	−0.001 (2)	0.001 (2)	0.0012 (17)
C2"	0.0284 (19)	0.0352 (18)	0.0210 (17)	0.0066 (15)	−0.0007 (14)	0.0079 (14)
C3"	0.033 (2)	0.0322 (18)	0.032 (2)	0.0021 (16)	−0.0019 (16)	0.0023 (15)
C4"	0.031 (2)	0.039 (3)	0.048 (3)	0.002 (2)	−0.006 (2)	0.000 (2)
O1'	0.063 (2)	0.0384 (16)	0.0367 (18)	0.0035 (15)	0.0194 (16)	0.0102 (13)
O2'	0.0443 (17)	0.0310 (13)	0.0225 (13)	−0.0037 (12)	−0.0010 (12)	0.0033 (10)

Geometric parameters (Å, º) top

C1'—C6'	1.389 (3)	C8—H83	0.9600
C1'—C2'	1.395 (3)	C9—C10	1.519 (2)
C1'—H1'	0.9300	C9—H91	0.9700
C2—N3	1.306 (2)	C9—H92	0.9700
C2—N1	1.3904 (19)	C10—C12	1.517 (3)
C2—S1	1.7537 (15)	C10—C11	1.540 (3)
C2'—C3'	1.413 (2)	C10—H10	0.9800
C2'—H2'	0.9300	C11—H111	0.9600
C3—O1	1.227 (2)	C11—H112	0.9600
C3—N1	1.398 (2)	C11—H113	0.9600
C3—C4	1.509 (2)	C12—H123	0.9600
C3'—C4'	1.393 (2)	C12—H121	0.9600
C3'—C7	1.524 (2)	C12—H122	0.9600
C4'—C5'	1.398 (3)	C41—O2	1.2394 (18)
C4'—H4'	0.9300	C41—N4	1.378 (2)
C4—H41	0.9600	C41—C42	1.508 (2)
C4—H42	0.9600	C42—H423	0.9600
C4—H43	0.9600	C42—H421	0.9600
C5—N4	1.4998 (19)	C42—H422	0.9600
C5—C9	1.524 (2)	N1—H1	0.8600
C5—C6	1.533 (2)	N3—N4	1.4058 (17)
C5—S1	1.8732 (15)	C1"—C2"	1.490 (6)
C5'—C6'	1.404 (3)	C1"—H13"	0.9600
C5'—H5'	0.9300	C1"—H12"	0.9600
C6'—C7'	1.521 (3)	C1"—H11"	0.9600
C6—C7	1.516 (2)	C2"—O1'	1.227 (5)
C6—H61	0.9700	C2"—O2'	1.358 (5)
C6—H62	0.9700	C3"—O2'	1.461 (5)
C7'—H71'	0.9600	C3"—C4"	1.470 (7)
C7'—H72'	0.9600	C3"—H32"	0.9700
C7'—H73'	0.9600	C3"—H31"	0.9700
C7—C8	1.539 (2)	C4"—H42"	0.9600
C7—H7	0.9800	C4"—H43"	0.9600
C8—H81	0.9600	C4"—H41"	0.9600
C8—H82	0.9600

C6'—C1'—C2'	120.88 (18)	H81—C8—H82	109.5
C6'—C1'—H1'	119.6	C7—C8—H83	109.5
C2'—C1'—H1'	119.6	H81—C8—H83	109.5
N3—C2—N1	119.84 (13)	H82—C8—H83	109.5
N3—C2—S1	119.38 (11)	C10—C9—C5	118.40 (13)
N1—C2—S1	120.77 (12)	C10—C9—H91	107.7
C1'—C2'—C3'	121.70 (16)	C5—C9—H91	107.7
C1'—C2'—H2'	119.2	C10—C9—H92	107.7
C3'—C2'—H2'	119.2	C5—C9—H92	107.7
O1—C3—N1	122.80 (14)	H91—C9—H92	107.1
O1—C3—C4	122.25 (15)	C12—C10—C9	107.44 (15)
N1—C3—C4	114.95 (14)	C12—C10—C11	109.96 (17)
C4'—C3'—C2'	117.43 (16)	C9—C10—C11	114.31 (16)
C4'—C3'—C7	120.79 (16)	C12—C10—H10	108.3
C2'—C3'—C7	121.74 (14)	C9—C10—H10	108.3
C3'—C4'—C5'	120.40 (18)	C11—C10—H10	108.3
C3'—C4'—H4'	119.8	C10—C11—H111	109.5
C5'—C4'—H4'	119.8	C10—C11—H112	109.5
C3—C4—H41	109.5	H111—C11—H112	109.5
C3—C4—H42	109.5	C10—C11—H113	109.5
H41—C4—H42	109.5	H111—C11—H113	109.5
C3—C4—H43	109.5	H112—C11—H113	109.5
H41—C4—H43	109.5	C10—C12—H123	109.5
H42—C4—H43	109.5	C10—C12—H121	109.5
N4—C5—C9	112.80 (13)	H123—C12—H121	109.5
N4—C5—C6	112.75 (12)	C10—C12—H122	109.5
C9—C5—C6	108.21 (12)	H123—C12—H122	109.5
N4—C5—S1	103.67 (9)	H121—C12—H122	109.5
C9—C5—S1	110.51 (11)	O2—C41—N4	120.49 (14)
C6—C5—S1	108.79 (11)	O2—C41—C42	121.15 (15)
C4'—C5'—C6'	122.16 (17)	N4—C41—C42	118.36 (13)
C4'—C5'—H5'	118.9	C41—C42—H423	109.5
C6'—C5'—H5'	118.9	C41—C42—H421	109.5
C1'—C6'—C5'	117.43 (18)	H423—C42—H421	109.5
C1'—C6'—C7'	120.3 (2)	C41—C42—H422	109.5
C5'—C6'—C7'	122.3 (2)	H423—C42—H422	109.5
C7—C6—C5	116.99 (12)	H421—C42—H422	109.5
C7—C6—H61	108.1	C2—N1—C3	124.63 (13)
C5—C6—H61	108.1	C2—N1—H1	117.7
C7—C6—H62	108.1	C3—N1—H1	117.7
C5—C6—H62	108.1	C2—N3—N4	110.27 (12)
H61—C6—H62	107.3	C41—N4—N3	119.50 (12)
C6'—C7'—H71'	109.5	C41—N4—C5	123.13 (12)
C6'—C7'—H72'	109.5	N3—N4—C5	117.36 (12)
H71'—C7'—H72'	109.5	C2—S1—C5	89.27 (7)
C6'—C7'—H73'	109.5	O1'—C2"—O2'	121.9 (4)
H71'—C7'—H73'	109.5	O1'—C2"—C1"	124.8 (4)
H72'—C7'—H73'	109.5	O2'—C2"—C1"	113.3 (4)
C6—C7—C3'	113.72 (14)	O2'—C3"—C4"	112.2 (4)
C6—C7—C8	108.77 (13)	O2'—C3"—H32"	109.2
C3'—C7—C8	110.65 (14)	C4"—C3"—H32"	109.2
C6—C7—H7	107.8	O2'—C3"—H31"	109.2
C3'—C7—H7	107.8	C4"—C3"—H31"	109.2
C8—C7—H7	107.8	H32"—C3"—H31"	107.9
C7—C8—H81	109.5	C2"—O2'—C3"	117.3 (3)
C7—C8—H82	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.95	2.812 (2)	179

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂
M_r	419.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	7.8713 (3), 12.7587 (5), 22.9688 (9)
β (°)	90.937 (2)
V (Å³)	2306.39 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.5 × 0.4 × 0.3

Data collection
Diffractometer	Bruker X8 APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27541, 7243, 6688
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.745

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.143, 1.23
No. of reflections	7243
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.35

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia,1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.95	2.812 (2)	179

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

We thank Professor Jean-Claude Daran, Laboratoire de Chimie de Coordination, Toulouse, France, for his fruitful help.

References

Abdou, N. A., Soliman, I. N. & Sier Abou, A. H. (1991). Bull. Facpharm. (Cairo Univ.), 28, 29. Google Scholar
Beatriz, N. B., Albertina, G. M., Miriam, M. A., Angel, A. L., Graciela, Y. M. & Norma, B. D. (2002). Arkivok, x, 14–23. Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Mohammed, T., Mazoir, N., Daran, J.-C., Berraho, M. & Benharref, A. (2008). Acta Cryst. E64, o610–o611. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sakthivel, P., Joseph, P. S., Muthiah, P. T., Sethusankar, K. & Thennarasu, S. (2008). Acta Cryst. E64, o216. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tehranchian, S., Akbarzadeh, T., Fazeli, R. M., Jamifar, H. & Shafiee, A. (2005). Bioorg. Med. Chem. Lett. 15, 1023–1025. Web of Science CrossRef PubMed CAS Google Scholar
Wang, Y.-G., Cao, L., Yang, J., Ye, W.-F., Zhou, Q.-C. & Lu, B.-X. (1999). Chem. J. Chin. Univ. 20, 1903–1905. CAS Google Scholar
Wang, Y.-G., Wang, Z. Y., Zhao, X. Y. & Song, X. J. (2004). Chin. J. Org. Chem. 24, 1606–1609. CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o4

doi:10.1107/S1600536808039998

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[4-Acetyl-5-iso­butyl-5-(2-p-tolyl­prop­yl)-4,5-di­hydro-1,3,4-thia­diazol-2-yl]acetamide ethyl acetate hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[4-Acetyl-5-isobutyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide ethyl acetate hemisolvate